This study was designed to investigate the impact of question prompts that guide students to focus on context-related issues when learning through cases in an ill-structured domain. Three groups of undergraduate students studied cases during a lab-session time period using a web-based environment. The first group studied without any question prompts. The second group studied the same material while prompted to provide written answers to embedded questions in the cases. The third group studied while having only to think of possible answers for the question prompts. In this study, we explored how the questioning intervention affected students' conceptual knowledge of the domain and their problem-solving ability. Post-tests did not reveal significant statistical differences in the groups' performance, indicating that under specific study conditions the prompting impact is not traceable in the learning outcomes. This result, however, is discussed in the light of a previous study, which showed that this context-oriented prompting method had a beneficial effect on student learning in a prolonged study-time setting, where students were able to self-regulate their study activity.